Waizumi Nobuaki, Stankovic Ana R, Rawal Viresh H
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637, USA.
J Am Chem Soc. 2003 Oct 29;125(43):13022-3. doi: 10.1021/ja035898h.
Described is an efficient synthesis of the complex bioactive natural product, elisapterosin B, a potent in vitro inhibitor of Mycobacterium tuberculosis H37Rb. The synthesis elisapterosin B, prepared in its enantiomeric form, proceeds by a highly stereocontrolled sequence commencing with a simple glutamic acid derived compound. Pivotal steps in the sequence include (a) a pinacol-type ketal rearrangement to transfer chirality, (b) an IMDA reaction of an E,Z-diene to construct the elisabethin skeleton, and (c) a biosynthesis-inspired oxidative cyclization of the elisabethin precursor to elisapterosin B.
本文描述了复杂生物活性天然产物elisapterosin B的高效合成方法，elisapterosin B是结核分枝杆菌H37Rb的一种有效的体外抑制剂。以对映体形式制备的elisapterosin B的合成，从一种简单的谷氨酸衍生化合物开始，通过高度立体控制的序列进行。该序列中的关键步骤包括：(a) 频哪醇型缩酮重排以转移手性；(b) E,Z-二烯的IMDA反应以构建elisabethin骨架；(c) 将elisabethin前体进行受生物合成启发的氧化环化反应生成elisapterosin B。
